NPASS Compound

Structure

NPC475484 OpenBabel07101718242D 41 44 0 0 1 0 0 0 0 0999 V2000 0.0000 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7709 -6.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2709 -5.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7709 -6.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7709 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7709 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 -1.7399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2709 -5.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -2.6910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2709 -5.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7709 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7709 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 -4.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2709 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3230 -0.9968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2709 -5.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2709 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2709 -5.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 -5.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2709 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 37 1 0 0 0 0 2 4 2 0 0 0 0 2 10 1 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 13 1 0 0 0 0 5 16 1 0 0 0 0 6 10 2 0 0 0 0 6 14 1 0 0 0 0 7 27 1 0 0 0 0 8 28 1 0 0 0 0 9 12 2 0 0 0 0 9 38 1 0 0 0 0 11 7 1 6 0 0 0 11 18 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 14 2 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 8 1 6 0 0 0 15 19 1 0 0 0 0 15 39 1 0 0 0 0 16 31 2 0 0 0 0 16 40 1 0 0 0 0 17 12 1 1 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 18 25 1 0 0 0 0 19 21 1 0 0 0 0 19 32 1 0 0 0 0 20 23 1 0 0 0 0 20 33 1 0 0 0 0 21 22 1 0 0 0 0 21 34 1 0 0 0 0 22 26 1 0 0 0 0 22 35 1 0 0 0 0 23 40 1 0 0 0 0 24 36 2 0 0 0 0 24 37 1 0 0 0 0 25 38 1 0 0 0 0 25 41 1 0 0 0 0 26 39 1 0 0 0 0 26 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.17
Volume:	537.424
LogP:	0.251
LogD:	-0.133
LogS:	-1.177
# Rotatable Bonds:	10
TPSA:	242.13
# H-Bond Aceptor:	15
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.089
Synthetic Accessibility Score:	5.091
Fsp3:	0.538
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.608
MDCK Permeability:	9.81375269475393e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.691
Human Intestinal Absorption (HIA):	0.935
20% Bioavailability (F20%):	0.484
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.216
Plasma Protein Binding (PPB):	52.15800094604492%
Volume Distribution (VD):	0.34
Pgp-substrate:	41.08122253417969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.041
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.04

ADMET: Excretion

Clearance (CL):	1.605
Half-life (T1/2):	0.973

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.15
Drug-inuced Liver Injury (DILI):	0.729
AMES Toxicity:	0.092
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.22
Carcinogencity:	0.266
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.435

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC475484

Natural Product ID:	NPC475484
*Common Name:**	Arbortristoside B
IUPAC Name:	methyl (1S,4aS,5S,6R,7S,7aS)-6-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-5-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Synonyms:
Standard InCHIKey:	PSFREQJZNFIHKK-OKPJLNDISA-N
Standard InCHI:	InChI=1S/C26H32O15/c1-37-24(36)12-9-38-25(41-26-22(35)21(34)19(32)15(8-28)39-26)18-11(7-27)23(20(33)17(12)18)40-16(31)5-3-10-2-4-13(29)14(30)6-10/h2-6,9,11,15,17-23,25-30,32-35H,7-8H2,1H3/b5-3+/t11-,15-,17-,18-,19-,20+,21+,22-,23-,25+,26+/m1/s1
SMILES:	OC[C@H]1[C@@H](OC(=O)/C=C/c2ccc(c(c2)O)O)[C@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506451
PubChem CID:	44576088
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33172	nyctanthes arbortristis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791475]
NPO33172	nyctanthes arbortristis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22608855]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	19

Activity Type	# Activity
Cell Line	2
Individual Protein	8
Organism	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	Activity	=	54.83	%	PMID[548377]
NPT71	Cell Line	HEK293	Homo sapiens	Activity	=	93.62	%	PMID[548377]
NPT6376	Individual Protein	Trypanothione reductase	Leishmania donovani	Inhibition	=	46.87	%	PMID[548377]
NPT6376	Individual Protein	Trypanothione reductase	Leishmania donovani	Inhibition	=	67.87	%	PMID[548377]
NPT6376	Individual Protein	Trypanothione reductase	Leishmania donovani	Inhibition	=	77.53	%	PMID[548377]
NPT6376	Individual Protein	Trypanothione reductase	Leishmania donovani	Inhibition	=	96.88	%	PMID[548377]
NPT6376	Individual Protein	Trypanothione reductase	Leishmania donovani	Inhibition	=	41.87	%	PMID[548377]
NPT6376	Individual Protein	Trypanothione reductase	Leishmania donovani	Inhibition	=	63.63	%	PMID[548377]
NPT6376	Individual Protein	Trypanothione reductase	Leishmania donovani	Inhibition	=	92.58	%	PMID[548377]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	28.13	%	PMID[548376]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	41.74	%	PMID[548376]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	25.12	%	PMID[548376]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	47.34	%	PMID[548376]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Survival	=	59.0	day	PMID[548376]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	7630.0	nM	PMID[548377]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	3504.0	nM	PMID[548377]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Activity	=	2.96	%	PMID[548377]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Activity	=	13.52	%	PMID[548377]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Activity	=	31.04	%	PMID[548377]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Activity	=	52.48	%	PMID[548377]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC475484 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	1166
0.2-0.3	2697
0.3-0.4	5254
0.4-0.5	9686
0.5-0.6	9456
0.6-0.7	9722
0.7-0.8	4013
0.8-0.85	288
0.85-0.9	62
0.9-0.95	22
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9592	High Similarity	NPC96599
0.9539	High Similarity	NPC179914
0.9396	High Similarity	NPC117346
0.9396	High Similarity	NPC240592
0.9355	High Similarity	NPC145847
0.9295	High Similarity	NPC109990
0.9252	High Similarity	NPC296659
0.9252	High Similarity	NPC202391
0.9226	High Similarity	NPC138993
0.9205	High Similarity	NPC475379
0.9122	High Similarity	NPC251062
0.9122	High Similarity	NPC184464
0.9108	High Similarity	NPC476011
0.9097	High Similarity	NPC187205
0.9079	High Similarity	NPC158546
0.9079	High Similarity	NPC289021
0.9062	High Similarity	NPC21956
0.9057	High Similarity	NPC130730
0.9057	High Similarity	NPC301910
0.9054	High Similarity	NPC186296
0.9032	High Similarity	NPC475378
0.902	High Similarity	NPC203664
0.9013	High Similarity	NPC69367
0.8986	High Similarity	NPC296643
0.8981	High Similarity	NPC474936
0.894	High Similarity	NPC18789
0.8919	High Similarity	NPC137501
0.8919	High Similarity	NPC7518
0.8919	High Similarity	NPC154262
0.8919	High Similarity	NPC159387
0.8868	High Similarity	NPC206815
0.8831	High Similarity	NPC269914
0.8831	High Similarity	NPC478249
0.8824	High Similarity	NPC478234
0.8824	High Similarity	NPC478236
0.8797	High Similarity	NPC469384
0.879	High Similarity	NPC478248
0.8784	High Similarity	NPC31745
0.8784	High Similarity	NPC220936
0.8774	High Similarity	NPC194705
0.8766	High Similarity	NPC147224
0.8734	High Similarity	NPC49173
0.8734	High Similarity	NPC286919
0.8734	High Similarity	NPC475663
0.8718	High Similarity	NPC229354
0.8718	High Similarity	NPC89693
0.8718	High Similarity	NPC229548
0.8718	High Similarity	NPC478241
0.8704	High Similarity	NPC282551
0.8658	High Similarity	NPC49597
0.8654	High Similarity	NPC478235
0.8636	High Similarity	NPC23677
0.8636	High Similarity	NPC308178
0.8627	High Similarity	NPC475539
0.8627	High Similarity	NPC473147
0.8627	High Similarity	NPC119773
0.8627	High Similarity	NPC473867
0.8627	High Similarity	NPC143246
0.8627	High Similarity	NPC474268
0.8618	High Similarity	NPC77922
0.8618	High Similarity	NPC473281
0.8618	High Similarity	NPC194938
0.8616	High Similarity	NPC104275
0.8616	High Similarity	NPC4747
0.8616	High Similarity	NPC226759
0.8608	High Similarity	NPC156624
0.8608	High Similarity	NPC172920
0.8599	High Similarity	NPC245615
0.8599	High Similarity	NPC115466
0.8599	High Similarity	NPC299706
0.8599	High Similarity	NPC61604
0.8581	High Similarity	NPC478242
0.8562	High Similarity	NPC76211
0.8562	High Similarity	NPC475528
0.8553	High Similarity	NPC475213
0.8553	High Similarity	NPC152796
0.8553	High Similarity	NPC293154
0.8544	High Similarity	NPC478232
0.8543	High Similarity	NPC46644
0.8533	High Similarity	NPC220942
0.8528	High Similarity	NPC180586
0.8526	High Similarity	NPC35097
0.8526	High Similarity	NPC12006
0.8516	High Similarity	NPC120728
0.8514	High Similarity	NPC169398
0.8509	High Similarity	NPC478265
0.8506	High Similarity	NPC212808
0.8497	Intermediate Similarity	NPC63304
0.8494	Intermediate Similarity	NPC470685
0.8491	Intermediate Similarity	NPC38699
0.8481	Intermediate Similarity	NPC44730
0.8471	Intermediate Similarity	NPC140151
0.8467	Intermediate Similarity	NPC302583
0.8467	Intermediate Similarity	NPC100558
0.8467	Intermediate Similarity	NPC84789
0.8467	Intermediate Similarity	NPC310252
0.8452	Intermediate Similarity	NPC473149
0.8446	Intermediate Similarity	NPC470143
0.8446	Intermediate Similarity	NPC322503
0.8438	Intermediate Similarity	NPC471405
0.8438	Intermediate Similarity	NPC163635
0.8431	Intermediate Similarity	NPC116104
0.8431	Intermediate Similarity	NPC263397
0.8431	Intermediate Similarity	NPC237872
0.8431	Intermediate Similarity	NPC302286
0.8431	Intermediate Similarity	NPC88754
0.8428	Intermediate Similarity	NPC191046
0.8428	Intermediate Similarity	NPC327032
0.8428	Intermediate Similarity	NPC194095
0.8428	Intermediate Similarity	NPC472128
0.8428	Intermediate Similarity	NPC472127
0.8411	Intermediate Similarity	NPC321184
0.8411	Intermediate Similarity	NPC321638
0.8411	Intermediate Similarity	NPC171134
0.8411	Intermediate Similarity	NPC472350
0.8411	Intermediate Similarity	NPC197316
0.8411	Intermediate Similarity	NPC89105
0.8411	Intermediate Similarity	NPC328273
0.8411	Intermediate Similarity	NPC81515
0.8411	Intermediate Similarity	NPC64141
0.8411	Intermediate Similarity	NPC476383
0.8411	Intermediate Similarity	NPC68092
0.8408	Intermediate Similarity	NPC229882
0.8408	Intermediate Similarity	NPC158635
0.84	Intermediate Similarity	NPC470572
0.8397	Intermediate Similarity	NPC28776
0.8397	Intermediate Similarity	NPC473138
0.8395	Intermediate Similarity	NPC130489
0.8395	Intermediate Similarity	NPC208676
0.8389	Intermediate Similarity	NPC287597
0.8389	Intermediate Similarity	NPC886
0.8389	Intermediate Similarity	NPC471883
0.8389	Intermediate Similarity	NPC34293
0.8385	Intermediate Similarity	NPC472860
0.8378	Intermediate Similarity	NPC473285
0.8375	Intermediate Similarity	NPC10205
0.8366	Intermediate Similarity	NPC477277
0.8366	Intermediate Similarity	NPC477278
0.8365	Intermediate Similarity	NPC157898
0.8365	Intermediate Similarity	NPC257847
0.8365	Intermediate Similarity	NPC87403
0.8354	Intermediate Similarity	NPC474620
0.8354	Intermediate Similarity	NPC100420
0.8344	Intermediate Similarity	NPC65262
0.8344	Intermediate Similarity	NPC92117
0.8344	Intermediate Similarity	NPC469364
0.8344	Intermediate Similarity	NPC260425
0.8344	Intermediate Similarity	NPC161955
0.8344	Intermediate Similarity	NPC476376
0.8344	Intermediate Similarity	NPC101686
0.8343	Intermediate Similarity	NPC475299
0.8333	Intermediate Similarity	NPC316539
0.8333	Intermediate Similarity	NPC123988
0.8333	Intermediate Similarity	NPC476870
0.8323	Intermediate Similarity	NPC478055
0.8323	Intermediate Similarity	NPC10945
0.8323	Intermediate Similarity	NPC108455
0.8323	Intermediate Similarity	NPC210330
0.8323	Intermediate Similarity	NPC228357
0.8322	Intermediate Similarity	NPC254398
0.8313	Intermediate Similarity	NPC208818
0.8313	Intermediate Similarity	NPC476364
0.8311	Intermediate Similarity	NPC254819
0.8311	Intermediate Similarity	NPC219677
0.8303	Intermediate Similarity	NPC475738
0.8302	Intermediate Similarity	NPC478268
0.8302	Intermediate Similarity	NPC36130
0.8302	Intermediate Similarity	NPC106818
0.8302	Intermediate Similarity	NPC134905
0.8301	Intermediate Similarity	NPC134405
0.8301	Intermediate Similarity	NPC9218
0.8301	Intermediate Similarity	NPC477279
0.8301	Intermediate Similarity	NPC476385
0.8301	Intermediate Similarity	NPC476377
0.8301	Intermediate Similarity	NPC47471
0.8299	Intermediate Similarity	NPC477293
0.8299	Intermediate Similarity	NPC229784
0.8299	Intermediate Similarity	NPC477294
0.8293	Intermediate Similarity	NPC41009
0.8291	Intermediate Similarity	NPC205054
0.8289	Intermediate Similarity	NPC205195
0.8284	Intermediate Similarity	NPC171706
0.8282	Intermediate Similarity	NPC239966
0.8282	Intermediate Similarity	NPC203020
0.828	Intermediate Similarity	NPC120621
0.828	Intermediate Similarity	NPC248257
0.8272	Intermediate Similarity	NPC133984
0.8269	Intermediate Similarity	NPC474234
0.8269	Intermediate Similarity	NPC37838
0.8266	Intermediate Similarity	NPC299855
0.8266	Intermediate Similarity	NPC96194
0.8261	Intermediate Similarity	NPC131532
0.8258	Intermediate Similarity	NPC196063
0.8258	Intermediate Similarity	NPC141455
0.8258	Intermediate Similarity	NPC296954
0.8258	Intermediate Similarity	NPC478240
0.8258	Intermediate Similarity	NPC229036
0.8258	Intermediate Similarity	NPC300894
0.8255	Intermediate Similarity	NPC473924
0.825	Intermediate Similarity	NPC137813

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC475484 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	749
0.2-0.3	1688
0.3-0.4	2668
0.4-0.5	2158
0.5-0.6	1195
0.6-0.7	365
0.7-0.8	52
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8896	High Similarity	NPD7685	Pre-registration
0.8411	Intermediate Similarity	NPD7266	Discontinued
0.8077	Intermediate Similarity	NPD6190	Approved
0.8035	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7228	Approved
0.7882	Intermediate Similarity	NPD3818	Discontinued
0.7798	Intermediate Similarity	NPD7199	Phase 2
0.7784	Intermediate Similarity	NPD6234	Discontinued
0.775	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7054	Approved
0.7697	Intermediate Similarity	NPD37	Approved
0.7688	Intermediate Similarity	NPD7472	Approved
0.7688	Intermediate Similarity	NPD7074	Phase 3
0.7669	Intermediate Similarity	NPD1653	Approved
0.7665	Intermediate Similarity	NPD4966	Approved
0.7665	Intermediate Similarity	NPD4967	Phase 2
0.7665	Intermediate Similarity	NPD4965	Approved
0.7665	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD230	Phase 1
0.7602	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7251	Discontinued
0.7543	Intermediate Similarity	NPD6797	Phase 2
0.7515	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD8127	Discontinued
0.7458	Intermediate Similarity	NPD7808	Phase 3
0.7453	Intermediate Similarity	NPD8166	Discontinued
0.7401	Intermediate Similarity	NPD7240	Approved
0.7394	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4628	Phase 3
0.7342	Intermediate Similarity	NPD6653	Approved
0.7325	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1934	Approved
0.7262	Intermediate Similarity	NPD7028	Phase 2
0.7261	Intermediate Similarity	NPD6663	Approved
0.7247	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD8455	Phase 2
0.7232	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5736	Approved
0.7222	Intermediate Similarity	NPD8312	Approved
0.7222	Intermediate Similarity	NPD8313	Approved
0.7213	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6559	Discontinued
0.7175	Intermediate Similarity	NPD7799	Discontinued
0.716	Intermediate Similarity	NPD4380	Phase 2
0.7159	Intermediate Similarity	NPD6166	Phase 2
0.7159	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2801	Approved
0.7135	Intermediate Similarity	NPD1465	Phase 2
0.7135	Intermediate Similarity	NPD5844	Phase 1
0.7119	Intermediate Similarity	NPD7473	Discontinued
0.711	Intermediate Similarity	NPD7075	Discontinued
0.7093	Intermediate Similarity	NPD3817	Phase 2
0.709	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6355	Discontinued
0.7055	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6005	Phase 3
0.7055	Intermediate Similarity	NPD5763	Approved
0.7055	Intermediate Similarity	NPD6002	Phase 3
0.7055	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5762	Approved
0.7055	Intermediate Similarity	NPD6004	Phase 3
0.7052	Intermediate Similarity	NPD3882	Suspended
0.7051	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5647	Approved
0.7045	Intermediate Similarity	NPD6232	Discontinued
0.7031	Intermediate Similarity	NPD7680	Approved
0.703	Intermediate Similarity	NPD4110	Phase 3
0.703	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3027	Phase 3
0.7024	Intermediate Similarity	NPD6273	Approved
0.702	Intermediate Similarity	NPD9545	Approved
0.7013	Intermediate Similarity	NPD9269	Phase 2
0.7006	Intermediate Similarity	NPD9494	Approved
0.7	Intermediate Similarity	NPD7458	Discontinued
0.7	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3620	Phase 2
0.6995	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD3094	Phase 2
0.6981	Remote Similarity	NPD3764	Approved
0.697	Remote Similarity	NPD6674	Discontinued
0.6936	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7819	Suspended
0.6933	Remote Similarity	NPD7033	Discontinued
0.6932	Remote Similarity	NPD5494	Approved
0.6928	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8150	Discontinued
0.6909	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1511	Approved
0.6897	Remote Similarity	NPD5353	Approved
0.6894	Remote Similarity	NPD1613	Approved
0.6894	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3751	Discontinued
0.6879	Remote Similarity	NPD6801	Discontinued
0.6871	Remote Similarity	NPD7097	Phase 1
0.6864	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD7435	Discontinued
0.6845	Remote Similarity	NPD7236	Approved
0.6839	Remote Similarity	NPD3705	Approved
0.6839	Remote Similarity	NPD3092	Approved
0.6828	Remote Similarity	NPD8434	Phase 2
0.6826	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1512	Approved
0.6821	Remote Similarity	NPD6385	Approved
0.6821	Remote Similarity	NPD6386	Approved
0.6821	Remote Similarity	NPD8320	Phase 1
0.6821	Remote Similarity	NPD8319	Approved
0.6802	Remote Similarity	NPD3455	Phase 2
0.68	Remote Similarity	NPD5402	Approved
0.6795	Remote Similarity	NPD1608	Approved
0.6792	Remote Similarity	NPD2861	Phase 2
0.679	Remote Similarity	NPD4140	Approved
0.679	Remote Similarity	NPD943	Approved
0.6772	Remote Similarity	NPD6362	Approved
0.677	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7497	Discontinued
0.6768	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD8151	Discontinued
0.6766	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7930	Approved
0.6765	Remote Similarity	NPD2533	Approved
0.6765	Remote Similarity	NPD2532	Approved
0.6765	Remote Similarity	NPD2534	Approved
0.676	Remote Similarity	NPD3787	Discontinued
0.6753	Remote Similarity	NPD9268	Approved
0.6748	Remote Similarity	NPD5735	Approved
0.6744	Remote Similarity	NPD7239	Suspended
0.6743	Remote Similarity	NPD5761	Phase 2
0.6743	Remote Similarity	NPD5760	Phase 2
0.6731	Remote Similarity	NPD1091	Approved
0.6728	Remote Similarity	NPD6233	Phase 2
0.6705	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6534	Approved
0.6702	Remote Similarity	NPD6535	Approved
0.6701	Remote Similarity	NPD6777	Approved
0.6701	Remote Similarity	NPD7999	Approved
0.6701	Remote Similarity	NPD6781	Approved
0.6701	Remote Similarity	NPD6779	Approved
0.6701	Remote Similarity	NPD6780	Approved
0.6701	Remote Similarity	NPD6778	Approved
0.6701	Remote Similarity	NPD6776	Approved
0.6701	Remote Similarity	NPD6782	Approved
0.6687	Remote Similarity	NPD826	Approved
0.6687	Remote Similarity	NPD825	Approved
0.6687	Remote Similarity	NPD2935	Discontinued
0.6684	Remote Similarity	NPD7296	Approved
0.6684	Remote Similarity	NPD7700	Phase 2
0.6684	Remote Similarity	NPD7699	Phase 2
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD6798	Discontinued
0.6667	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7874	Approved
0.665	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD447	Suspended
0.6646	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1357	Approved
0.6644	Remote Similarity	NPD3022	Approved
0.6644	Remote Similarity	NPD3021	Approved
0.663	Remote Similarity	NPD5242	Approved
0.6629	Remote Similarity	NPD7411	Suspended
0.6627	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1510	Phase 2
0.6627	Remote Similarity	NPD3750	Approved
0.6617	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7783	Phase 2
0.6608	Remote Similarity	NPD6799	Approved
0.6607	Remote Similarity	NPD1549	Phase 2
0.6605	Remote Similarity	NPD7095	Approved
0.6603	Remote Similarity	NPD17	Approved
0.6603	Remote Similarity	NPD3019	Approved
0.6603	Remote Similarity	NPD2932	Approved
0.6599	Remote Similarity	NPD7696	Phase 3
0.6599	Remote Similarity	NPD7697	Approved
0.6599	Remote Similarity	NPD7698	Approved
0.659	Remote Similarity	NPD5403	Approved
0.6587	Remote Similarity	NPD2438	Suspended
0.6587	Remote Similarity	NPD9570	Approved
0.6587	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6099	Approved
0.6587	Remote Similarity	NPD6100	Approved
0.6585	Remote Similarity	NPD4060	Phase 1
0.6584	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD3091	Approved
0.6576	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7229	Phase 3
0.6571	Remote Similarity	NPD6599	Discontinued
0.657	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD1652	Phase 2
0.6566	Remote Similarity	NPD7870	Phase 2
0.6566	Remote Similarity	NPD7871	Phase 2
0.6562	Remote Similarity	NPD6213	Phase 3
0.6562	Remote Similarity	NPD6212	Phase 3
0.6562	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6765	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data